The study sought to examine school administrators' engagement in the reintegration of students in schools during the pandemic era. The study was conducted using a multiple case study design that used an open-ended survey design to collect data from the selected school administrators. A total of eight participants were selected using a purposive sampling technique. The results of the study found that several challenges such as disruptions, indiscipline, fights, abnormal behaviors, and inadequate support structures all affected the reintegration process of students during the COVID-19 pandemic era.